I really don't see Pierce doing this after he's retired. For one thing, I think he'll probably live full time back on the west coast. Also, it's not that glamorous a job. You have to travel with the team and be away from your family just like you were when you were playing. Only difference, you're not playing anymore and not getting paid nearly as much.
When you think of former players that do it, like Cedric Maxwell, it's not as if these guys are set for life and can just retire. I can guarantee you Pierce made more money just off his rookie contract than Maxwell made his whole career.
But a lot of former players do miss the spotlight, and since basketball has been there life for so long, it's hard to give it up. So in that regard, it's always a possibility. But it would definitely be t.v. before radio for Pierce.